Older Woman Got My Cherry.....

     Here’s a true story that happened to me some time ago. I used to hang around a guy’s shop on the weekends. I would help him out on the counter, and he would let me work on my hot rod in the shop. He didn’t pay me anything. I just liked hanging out there.

     I was there on a Saturday doing something on my car when he came into the back of the shop along with an older woman. She might have been early to mid-thirties and not bad looking. He said, “Hey Jack, I’ve been telling my friend Linda that you’re still a virgin and that somebody needs to take your cherry and she’s volunteered.”

     I don’t mind telling you that this shocked the crap out of me. I really didn’t know what the hell to say but it seemed like a good idea. She got very friendly and invited me into the back seat of large 4-door Cadillac that was in the shop. The shop owner went back to the retail store portion of the shop and left us alone.

     She started telling me what to do. First she told me to get undressed, which was a bit of a production since I had coveralls over the top of my regular clothes. I got the coveralls off and she unzipped my pants and got my cock out which was already rock hard in anticipation. She was wearing a skirt and blouse. She hiked up her skirt and pulled off her panties and tossed them aside. She unbuttoned her blouse and got one tit out of her brassiere and told me to suck her nipple. She grabbed my cock and started jacking me off. I warned her not to go too fast because being a kid, I might shoot my load too quickly. 

     We played around with some foreplay with her instructing me every step of the way. Finally, she told me to penetrate her. I fumbled around trying to find her slit without much luck. She got a little annoyed and grabbed my dick and guided it into her vagina. Once in I knew what to do and started ramming it home. She was panting and groaning and humping back at me saying, “Fuck me, fuck the shit out of me, cum in me….” Which I proceeded to do. 

     Before too long, the inevitable happened and I dropped a big load of cum in her pussy. We laid there for a while and my dick got soft and slipped out of her cunt. We kind of put ourselves back together. I had a shop rag (fortunately, a clean one) in my coveralls pocket, and I wiped my dick off as it was coated in her juices and my cum. 

     We got out of the car and she asked me what I thought, and I told her it was one of the greatest experiences of my life. She asked me how old I was, and I told her I was 17. She seemed satisfied and left. I asked the shop owner what the deal was, and he said she was just an old girlfriend who was always horny and loved to fuck. 

     Now let me tell you the whole truth. I’ve always looked way younger than my age. At the time this occurred I was 26 years old, married for five years with three kids and at that point had probably fucked about ten different women. But I did look about 17 or 18. The shop owner knew all of this, of course, and thought the whole thing was hilarious. I always wondered if he ever told her the actual facts. I never saw her again, but it was a very memorable experience. It wasn’t a high-quality fuck but because of the unusual circumstances, it’s certainly one I will always remember.